Rain on the Skylight


It’s the first week of January at something like 3 am. I was thinking about a friend of mine I last heard from thirty-eight years ago today. We lost touch because of bad travel plans. I shouldn’t have given up so soon. I should have been more combative, more pessimistic. What an optimistic ass I was back then. That’s not always a good thing.

But it got me thinking here in the witching hours of night, of those times and what I did and what I failed to do. Such as, I should have kept playing tennis.

I should have kept playing guitar.

I should have stayed in Massachusetts.

I should have headed to USC for that Film School thing after college.

I should have taken that job tending bar in the Austrian castle.

I hate three am.

Anyone ever do this? Not seriously, not in a regretful way really, but those witching-hour moments of, what is it? Not self-doubt, really. More of a review; an analysis of “me so far.” The moments don’t linger; I don’t stop on the Massachusetts one and get frustrated at all that might have happened if I stayed or what could have been avoided, no. It’s just a “wow, of all the places I’ve lived I wish I had stayed there.” Really, no big deal. This isn’t a “My Regrets” blog by any means. It is an exercise in nature where the view is hindsight and the wilderness is disparity. As for Massachusetts, I quickly recall trying to drive Route 140 up the mountain in winter, and the moment passes, and I realize I should have moved to Florida.

Instead of Penn State I should have gone to NYU. I was accepted at both, but I didn’t think I could afford New York. As it turns out I couldn’t afford Pennsylvania either so I should have not afforded New York instead. While there, I should have joined my old friend Sean who is an actor in NY and gone to some casting calls. I always wanted to play the dead body at the beginning of “Law and Order.” Or I could have taken advantage of the NY City nightclub scene and done stand up. But I’m seriously certain I wasn’t funny enough. Not yet. Age provides humor.

See, this reflection isn’t serious. Not really. But it’s late, and I’m tired, so I think sometimes about the downside, the shadowy side of it all, like how I should have answered the phone that morning in ’92 when I sat staring at the desk in my office thinking how I should have stayed in bed, that I didn’t want to talk to anyone. Not yet. And how a few days later I should have apologized to his father at the funeral when all I told him was that I should have called more often.

Time passes and I should have gone to Monterey anyway. I should have tried harder or given up completely. They’re so closely related, quitting and devotion. I should have learned the difference. Maybe I already knew I shouldn’t go and that thirty years later it would all make sense. Or maybe I simply couldn’t afford it, financially or emotionally. I should have learned to invest in both. I did some math: If I had saved one dollar a day from the time I was born I’d have roughly $22 thousand dollars right now. That’s a new Civic. I could have had a new Civic. I should have done that.

I am going to be sixty and I’ve been really tired, just really tired. It’s not depression, really, and my doctor says it is not chemical, it’s situational. I should have found a different doctor. Or maybe I should have found a therapist. Like that one who always finishes my sentences, who I can be around and be quiet a long time without being asked, “So what’s wrong you’ve been quiet?” But I don’t think she’s licensed. I should have majored in philosophy. Or psychology. Or journalism. Well, okay, but I should have actually pursued a career in my major instead of, you know, not.

I didn’t know I was wrong, or right, or on the wrong or right path. I didn’t have that kind of sense of things back then. Or now I suppose. I didn’t know a good coach would have made all the difference. No one ever said, “You really need some better coaches; you can make this happen.” I grew up in a time when as long as you weren’t in trouble nothing needed to be talked about. This was not the age of trophies for everyone and helicopter parents. Life was fine so long as I wasn’t in trouble. But that’s the thing; I was always hanging out at the beach, walking instead of being on the court, being on the ball, being in the books, being aware of what was next, aware of what to do. And when you’re just not sure what to do, you do nothing. It’s that simple.

I shouldn’t have done nothing.

I should never have quit piano lessons. Four days was simply not long enough.

I should have stayed in Spain.


Less than two years ago I left a job I held for three decades.

Truth be told, I now know what I should have done differently: I should have left sooner. I should have abandoned a job I had no business doing to begin with and pursed something creative years earlier. I got hooked by the security and respectability and money, but I was never really qualified to teach what I taught. On paper, sure, but life is not paper, life is not degrees, life is not always expectations and responsibilities and duty. Those things are important, yes, of course, and before my note section here fills up with how wrong I am I should point out I do have three college degrees, I was responsible enough to hold down an incredibly respectable job for thirty years, and I always showed up. Always.

But that is not life. That is not passion. That is not what sets the soul on fire and ignites that internal motivation. I spent a few days with a pretty popular recording artist once when I was a senior at college. We sat one afternoon playing guitars and he asked what my major was, and he asked why the hell I wasn’t involved more in music. “You should finish school and then forget it and get into this. You really should,” he said.

I shouldn’t have spent any time with him. That just fucked with my head.

Explain this: I had that one job since the end of the Reagan administration to the second year of the current chaos in DC—I taught English, college comp, etc., but I had NO English training AT ALL—honest, none. My degrees at the time were in journalism, and then humanities and art, not English. On top of that, I had never taught a class in my life except for Richard Simmons, and that wasn’t college, it was loud music and fifty people sweating their asses off, literally. On paper, fine, they said. But I walked into the classroom that first time and for quite some years after and basically taught senior-level journalism.  Sure, eventually I received a terminal degree, this time in English, creative writing, etc, so I did work until I knew what I was doing. But it was such a relief when I left; I felt like no matter how hard things can get without that security, I just stepped out of something vague and unhealthy and into the reality of life where you can feel your pulse, you can feel your desire like something stirring in your stomach. On top of that I spent thirty years there and I haven’t heard from one person since I left. I was never so isolated as when I was there. Yes, by God, I should have left sooner.

But then, Spain. So listen: after you fall to sleep and have gone through your “I shouldn’t have’s” and your “I should have’s,” do you recall the one moment that you know you can land on if you’re falling? That one time or person or place in your life that retains such clarity and focus, that you can go there—physically or mentally—and you know you will step back into purpose and direction again?

For me, Spain.

No, this isn’t about going back to Spain, though I will, or walking the Camino again, though I will. It is about remembering that this pilgrimage we’re on is laced with “I should have stopped earlier, I should have kept going, I should have turned there and left sooner and on and on and on.” Oh to complete that pilgrimage taught me about this grander journey, and I wish I had done it when I was my son’s age when he did it; they don’t teach pilgrimage in school. They don’t teach so many things about life, like how to recognize you’re still too young to recognize what is permanent and what is fleeting. They don’t teach you when to forget about who’s missing and when to head out and see for yourself; they don’t teach you when to answer the phone, when to change courses, not to read Frost, to read more Rumi. They don’t teach you so much. I shouldn’t have expected to simply know everything I needed to know. They don’t teach you just how ignorant you are; they tell you how smart you are, and then they send you out to discover on your own your shortcomings. That’s fair, I suppose, but they could have at least warned us, right? They could have an exam in some civics course entitled, “Someday at three am you’re going to wake up and wonder about all the things you shouldn’t have done. Have a blue book and a number two pencil ready.”

I don’t think people think about this. Or maybe they do and I’m just catching on, late as usual. Well, we all should believe in ourselves earlier.

Anyway, what I was about to write before Truth interrupted with all her matter of factness about Robert Frost and wrong paths and three am, there are so many things not that I wish I had done but that I wish I hadn’t. But really, at the end of the end, I will be more regretful of what I wanted to do and didn’t try than what I did do and failed.

I really wish I could talk to my dad right now. Have a Scotch. He was an example of such unparalleled strength. He didn’t offer advice, not really. Maybe my siblings remember him doing so, but I don’t. But, man, he was an amazing example of what a person should be in the best of circumstances. I miss his strong, quiet presence. I should have been more like him.


Something has got to change. And apparently it isn’t going to be anyone else, or the world, or the menu at Panera, so it is going to have to be me. Maybe intelligence isn’t simply knowing when to show up but knowing when to leave. Sometimes we learn late, but, well, we do learn.

I shouldn’t have had so many Cheez-Its before bed. I should have stopped at one coconut rum and orange juice.

I should get back in bed and try and sleep. And when someone says, “Well, you’re doing the best you can,” I should stop them and say, “How do you know?” Honest to God, stop telling people that. How do you know??

No. I’m not. And it is usually only at this hour of the night that I am blatantly aware of that fact; that I absolutely am not doing the best that I can. Are you? Does anyone? How do we know? Think about it, how do we measure what we are capable of? To each other? No, of course not. To past performance? I hope not. Then how? Instinct? Faith?

Damn. Now I’m awake again.

I should have gone to bed two paragraphs ago. I should go downstairs and get some Oreos. I shouldn’t have…


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